The synthesis of 17-alkoxycarbonyl- and 17-carboxamido-13α-estra-1,3,5(10),16-tetraene derivatives via palladium-catalyzed carbonylation reactions

Steroids

Volumn 73, Issue 6, 2008, Pages 669-675

  Ács, Péter ^a   Takács, Attila ^a   Szilágyi, Antal ^a   Wölfling, János ^b   Schneider, Gyula ^b   Kollár, László ^a  

^a UNIVERSITY OF PÉCS   (Hungary)

^b UNIVERSITY OF SZEGED   (Hungary)

Author keywords

13 Steroid; Carbonylation; Carboxamide; Iodo alkene; Palladium

Indexed keywords

17 ALKOXYCARBONYL 13ALPHA ESTRA 1,3,5(10),16 TETRAENE DERIVATIVE; 17 CARBOXAMIDO 13ALPHA ESTRA 1,3,5(10),16 TETRAENE DERIVATIVE; 17 ESTER; AMIDE; ESTER; IODINE; METHANOL; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CARBONYLATION; CATALYSIS; CHEMICAL REACTION; SYNTHESIS;

CATALYSIS; ESTRONE; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; PALLADIUM;

EID: 41549159199     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2008.02.002     Document Type: Article

References (24)

1. Butenandt A., Wolff A., and Karlsson P. Über Lumi-oestron. Ber Dtsch Chem Ges 74 (1941) 1308-1312
2. Nambara T., Kudo T., Hosoda H., Motojima K., and Goya S. Conformational analysis of epimeric 16-bromo-13α-estrones. Chem Pharm Bull 17 (1969) 2366-2370
3. Nambara T., and Kudo T. The synthesis and conformational analysis of α-bromo-16-ketones of 13α-estratriene. Chem Pharm Bull 20 (1972) 2156-2162
4. Nambara T., Hosoda H., and Usui M. A nuclear magnetic resonance spectral study of 5α, 13α-androstanes. Chem Pharm Bull 17 (1969) 1687-1693
5. Nambara T., Kudo T., Hosoda H., Iitaka Y., and Kikutani N. Analytical chemical studies on steroids. 77. Crystal structure of 3-methoxy-16-hydroxy-13-alpha-estra-1,3,5(10),15-tetraen-17-one para-bromobenzoate. Chem Pharm Bull 23 (1975) 320-325
6. Schönecker B., Lange C., Kötteritzsch M., Günther W., Weston J., Anders E., et al. Conformational design for 13α-steroids. J Org Chem 65 (2000) 5487-5497
7. Skoda-Földes R., and Kollár L. Transition-metal-catalyzed reactions in steroid synthesis. Chem Rev 103 (2003) 4095-4129
8. Holt DA, Levy MA, Metcalf BW. Inventors; SmithKline Beecham Co.; EP 0 343 954 A2, 1989 (Chem Abstr 1990;112:198890n).
9. Cacchi S., Ciattini P.G., Morera E., and Ortar G. Palladium-catalyzed carbonylation of aryl triflates. Synthesis of arenecarboxylic acid derivatives from phenols. Tetrahedron Lett 27 (1986) 3931-3934
10. Dolle R.E., Schmidt S.J., and Kruse L.I. Palladium catalysed alkoxycarbonylation of phenols to benzoate esters. Chem Commun (1987) 904-905
11. Holt D.A., Levy M.A., Ladd D.L., Oh H., Erb J.M., Heaslip J.I., et al. Steroidal A ring aryl carboxylic acids: a new class of steroid 5α-reductase inhibitors. J Med Chem 33 (1990) 937-942
12. Tian W., Lei Z., Chen L., and Huang Y. Some new reactions of poly(per)fluoroalkanesulfonyl fluorides with steroidal molecules. J Fluorine Chem 101 (2000) 305-308
13. McGuire M.A., Sorenson E., Klein D.N., and Baine N.H. Palladium and nickel catalyzed hydroxycarbonylation of a steroidal bromodiene in the synthesis of episteride, a potent 5α-reductase inhibitor. Synth Commun 28 (1998) 1611-1615
14. Petz A., Gálik G., Horváth J., Tuba Z., Berente Z., Pintér Z., et al. Facile, high-yielding synthesis of steroidal crown ethers via palladium-catalysed carbonylation reaction. Synth Commun 31 (2001) 335-341
15. Ács P., Müller E., Czira G., Mahó S., Pereira M., and Kollár L. Facile synthesis of 12-carboxamido-11-spirostenes via palladium-catalyzed carbonylation reactions. Steroids 71 (2006) 875-879
16. Ács P., Jakab B., Takács A., and Kollár L. Facile synthesis of 11-carboxamido-androst-4,9(11)-dienes via palladium-catalyzed aminocarbonylation. Steroids 72 (2007) 627-632
17. Mernyák E., Wölfling J., Bunkóczi G., Luo L., Schneider T.R., and Schneider G. Stereoselective synthesis of the two trans-(16-hydroxymethyl)-3-methoxy-13α-estra-1,3,5(10)-trien-17-ol isomers. Coll Czech Chem Commun 68 (2003) 1141-1148
18. di Chenna P.H., Ferrara A., Ghini A.A., and Burton G. Cleavage of cyclopropyl ketones mediated by alkylmercury(II) hydrides. J Chem Soc Perkin Trans 1 (2002) 227-231
19. Sondheimer F., Baters E., and Rosenkranz G. Steroids. LXXXVI. Synthesis of monofunctional 11-ketones. J Am Chem Soc 70 (1948) 1090-1092
20. Barton D.H.R., O'Brien R.E., and Sternhell S. A new reaction of hydrazones. J Chem Soc (1962) 470-476
21. Barton D.H.R., Bashiardes B., and Fourrey J.L. An improved preparation of vinyl iodides. Tetrahedron Lett 24 (1983) 1605-1608
22. Csákai Z., Skoda-Földes R., and Kollár L. NMR investigation of Pd(II)-Pd(0) reduction in the presence of mono- and ditertiary phosphines. Inorg Chim Acta 286 (1999) 93-97 [and references cited therein]
23. Mernyák E., Schneider G., Herbst-Irmer R., Kubas M., and Wölfling J. Synthesis and stereochemical investigations of novel nitrogen-containing 13α-estrone derivatives. Steroids 71 (2006) 558-564
24. Bunkóczi G., Cuesta Seijo J.A., Szájli A., Schneider G., and Wölfling J. 3β-Acetoxy-13α-androst-5-en-17-one. Acta Cryst C (2006) o5078-o5079